scholarly journals Design, synthesis and antimycobacterial evaluation of some new azaheterocycles with the 4,7-phenanthroline skeleton. Part VI

2016 ◽  
Vol 81 (2) ◽  
pp. 133-140 ◽  
Author(s):  
Matarneh Al ◽  
Catalina Ciobanu ◽  
Ionel Mangalagiu ◽  
Ramona Danac
Keyword(s):  
Antimycobacterial Activity ◽  
Alkylation Reaction ◽  
Design Synthesis ◽  
1H And 13C Nmr ◽  
Mycobacterium Tuberculosis H37rv ◽  
13C Nmr Analysis ◽  
New Compounds ◽  
Feasible Study ◽  
Influence Of Substituents

A feasible study concerning the synthesis, structure and in vitro antimycobacterial evaluation of new 4,7-phenanthroline derivatives is reported. The preparation is straight and efficient, involving an N-alkylation reaction of 4,7-phenanthroline. The structure of the new compounds have been proved by elemental and spectral (IR, 1H and 13C NMR) analysis. The in vitro antimycobacterial evaluation of five synthesized compounds was investigated against Mycobacterium tuberculosis H37Rv under aerobic conditions. A certain influence of substituents from the para position of the benzoyl moiety was observed, the 4,7-phenanthrolin-4-ium salt substituted with (p)chloro-benzoyl showing the most pronounced antimycobacterial activity.

scholarly journals Design, Synthesis and Evaluation of N-pyrazinylbenzamides as Potential Antimycobacterial Agents

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2390 ◽  
Author(s):  
Jan Zitko ◽  
Alžběta Mindlová ◽  
Ondřej Valášek ◽  
Ondřej Jand’ourek ◽  
Pavla Paterová ◽  
...  
Keyword(s):  
Benzene Ring ◽  
Biological Activities ◽  
Clinical Importance ◽  
Antimycobacterial Activity ◽  
Substitution Pattern ◽  
Design Synthesis ◽  
Fungal Strains ◽  
Mycobacterium Tuberculosis H37rv ◽  
Homo And Lumo

Three series of N-(pyrazin-2-yl)benzamides were designed as retro-amide analogues of previously published N-phenylpyrazine-2-carboxamides with in vitro antimycobacterial activity. The synthesized retro-amides were evaluated for in vitro growth inhibiting activity against Mycobacterium tuberculosis H37Rv (Mtb), three non-tuberculous mycobacterial strains (M. avium, M. kansasii, M. smegmatis) and selected bacterial and fungal strains of clinical importance. Regarding activity against Mtb, most N-pyrazinylbenzamides (retro-amides) possessed lower or no activity compared to the corresponding N-phenylpyrazine-2-carboxamides with the same substitution pattern. However, the active retro-amides tended to have lower HepG2 cytotoxicity and better selectivity. Derivatives with 5-chloro substitution on the pyrazine ring were generally more active compared to their 6-cloro positional isomers or non-chlorinated analogues. The best antimycobacterial activity against Mtb was found in N-(5-chloropyrazin-2-yl)benzamides with short alkyl (2h: R2 = Me; 2i: R2 = Et) in position 4 of the benzene ring (MIC = 6.25 and 3.13 µg/mL, respectively, with SI > 10). N-(5-Chloropyrazin-2-ylbenzamides with hydroxy substitution (2b: R2 = 2-OH; 2d: R2 = 4-OH) on the benzene ring or their acetylated synthetic precursors possessed the broadest spectrum of activity, being active in all three groups of mycobacterial, bacterial and fungal strains. The substantial differences in in silico calculated properties (hydrogen-bond pattern analysis, molecular electrostatic potential, HOMO and LUMO) can justify the differences in biological activities between N-pyrazinylbenzamides and N-phenylpyrazine-2-carboxamides.

scholarly journals Synthesis and selective antitubercular and antimicrobial inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazole derivatives

2006 ◽  
Vol 71 (7) ◽  
pp. 713-720 ◽  
Author(s):  
P.T. Chovatia ◽  
J.D. Akabari ◽  
P.K. Kachhadia ◽  
P.D. Zalavadia ◽  
H.S. Joshi
Keyword(s):  
Hydrazine Hydrate ◽  
Antimycobacterial Activity ◽  
Antimicrobial Activities ◽  
Proteus Vulgaris ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Mycobacterium Tuberculosis H37rv ◽  
Aryl Ketones ◽  
New Compounds

The new compounds 1-aryl-3-{1-phenyl-3-[p (methylthio)phenyl]pyrazol-4-yl}-2-propen-1-ones 2a?l were prepared by the condensation of 1-phenyl-3-[p (methylthio)phenyl]-4-formylpyrazole 1 with different aryl ketones. Compounds 2a?l in reaction with hydrazine hydrate yielded 3-aryl-5-{1-phenyl-3-[p-(methylthio)phenyl]pyrazol-4 yl}-4,5-dihydro-(1H)-pyrazoles 3a?l and in the presence of hydrazine hydrate in glacial acetic acid gave 1-acetyl-3-aryl 5-{1-phenyl-3-[p-(methylthio)phenyl]pyrazol-4-yl}-4,5 dihydro-(1H)-pyrazoles 4a?l. These compounds were tested in vitro for their antitubercular and antimicrobial activities. The in vitro antimycobacterial activity of the newly synthesized compounds was investigated against Mycobacterium tuberculosis H37RV (ATCC 27294) in BACTEC 12B medium using the ALAMAR radiometric system. The antimicrobial in vitro activity was tested against Bacillus coccous, Bacillus subtilis Escherichia coli, Proteus vulgaris and antifungal activity against Aspergillus niger. The structures of the synthesized compounds were assigned on the basis of elemental analysis IR, 1H NMR and mass spectral data.

Design, Synthesis and Evaluate In Vitro Antifungal Activity of Novel Benzamide Derivatives

2019 ◽  
Vol 41 (3) ◽  
pp. 549-549
Author(s):  
Xuesong Wang and Xiaorong Tang Xuesong Wang and Xiaorong Tang
Keyword(s):  
Antifungal Activity ◽  
Pathogenic Fungi ◽  
Gibberella Zeae ◽  
Design Synthesis ◽  
Carboxylic Acid Amides ◽  
Almost All ◽  
Negative Controls ◽  
New Compounds ◽  
Benzamide Derivatives

A series of novel benzamide derivatives according to fluopicolide were designed and synthesized following the rule of combination carboxylic acid amides and amines derivatives together. The antifungal activity of the 15 new compounds were evaluated in vitro against five pathogenic fungi, including Sclerotinia sclerotiorum, Gibberella zeae, Rhizoctonia solani, Helminthosporium maydis and Botrytis cinerea. Almost all the structure have not been reported, except compounds 3, 5 and 6. A surprising finding is that all the five tested fungi breed faster than negative controls when supplementary with compound 715 , respectively.

Synthesis,Characterization and Evaluation of Biological Activity of Sulfonylhydrazide-Schiff Base" (E)- N’-(2,5-dimethoxybenzalidene) naphthalene-2-sulfonohydrazide"

2020 ◽  
Vol 8 (1) ◽  
pp. 01-11
Author(s):  
Sameer Amereih ◽  
Abd Daraghmeh ◽  
Ismail Warad ◽  
Mohammed Al-Nuri
Keyword(s):  
Schiff Base ◽  
Inhibitory Concentration ◽  
Condensation Reaction ◽  
Gram Negative Bacteria ◽  
Biological Applications ◽  
Bacteriostatic Effect ◽  
1H And 13C Nmr ◽  
13C Nmr Analysis ◽  
Ft Ir

Condensation reaction of naphthalene -2-Sulfonylhydrazide, as starting material with 2,5-dimethoxy benzaldehyde was used to produce (E)-N’-(2,5-dimethoxybenzalidene)naphthalene-2-sulfonohydrazide. The Schiff base product was isolated, purified and then spectrally characterized via UV-Vis, GC/MS, FT-IR, 1H and 13C NMR analysis, where strong evidences confirmed the formation of the desired product. Antimicrobial activity of Schiff base product was evaluated in vitro against several types of bacteria such as: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae and MRSA by Minimum Inhibitory Concentration (MIC) test using tetracycline (TE) as a standard antibiotic. The tests showed a promising bacteriostatic effect of this compound against gram negative bacteria such as P. aeruginosa and K. pneumoniae, such character is valuable for biological applications.

scholarly journals Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5852
Author(s):  
Hui Bai ◽  
Xuelian Liu ◽  
Pengfei Chenzhang ◽  
Yumei Xiao ◽  
Bin Fu ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Binding Modes ◽  
Oxime Ether ◽  
Single Crystal Diffraction ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives ◽  
Pyridine Moiety ◽  
New Compounds

A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a18) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a4) exhibited a broad-spectrum antifungal activities with the EC50 values of 1.59, 0.46, 0.27 and 11.39 mg/L against S. sclerotiorum, P. infestans, R. solani and B. cinerea, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (5b2) provided the lowest EC50 value of 0.12 mg/L against S. sclerotiorum, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds 5a4 and 5b2 with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides.

scholarly journals Design, Synthesis and Biological Evaluation of Novel 4-Substituted Coumarin Derivatives as Antitumor Agents

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2281 ◽  
Author(s):  
Ran An ◽  
Zhuang Hou ◽  
Jian-Teng Li ◽  
Hao-Nan Yu ◽  
Yan-Hua Mou ◽  
...  
Keyword(s):  
Antitumor Agents ◽  
Cancer Cell Line ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Hypoxic Conditions ◽  
Ca Ix ◽  
Ic50 Value ◽  
Almost All ◽  
New Compounds

Herein, fifteen new compounds containing coumarin, 1,2,3-triazole and benzoyl- substituted arylamine moieties were designed, synthesized and tested in vitro for their anticancer activity. The results showed that all tested compounds had moderate antiproliferative activity against MDA-MB-231, a human breast cancer cell line, under both normoxic and hypoxic conditions. Furthermore, the 4-substituted coumarin linked with benzoyl 3,4-dimethoxyaniline through 1,2,3-triazole (compound 5e) displayed the most prominent antiproliferative activities with an IC50 value of 0.03 μM, about 5000 times stronger than 4-hydroxycoumarin (IC50 > 100 μM) and 20 times stronger than doxorubicin (IC50 = 0.60 μM). Meanwhile, almost all compounds revealed general enhancement of proliferation-inhibiting activity under hypoxia, contrasted with normoxia. A docking analysis showed that compound 5e had potential to inhibit carbonic anhydrase IX (CA IX).

scholarly journals Design, Synthesis, andIn VitroAntiplatelet Aggregation Activities of Ferulic Acid Derivatives

2015 ◽  
Vol 2015 ◽  
pp. 1-7 ◽  
Author(s):  
Peng-Xuan Zhang ◽  
Hang Lin ◽  
Cheng Qu ◽  
Yu-Ping Tang ◽  
Nian-Guang Li ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Target Compound ◽  
Design Synthesis ◽  
Antiplatelet Aggregation ◽  
Aggregation Activity ◽  
New Compounds

In order to discover new compounds with antiplatelet aggregation activities, some ferulic acid (FA) derivatives were designed and synthesized. Thein vitroantiplatelet aggregation activities of these compounds were assessed by turbidimetric test. The results showed that the target compound7fhad potent antiplatelet aggregation activity with its IC5027.6 μmol/L, and7fcan be regarded as a novel potent antiplatelet aggregation candidate.

scholarly journals Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety

2019 ◽  
Vol 70 (4) ◽  
pp. 1099-1107
Author(s):  
Theodora-Venera Apostol ◽  
Stefania-Felicia Barbuceanu ◽  
Octavian Tudorel Olaru ◽  
Constantin Draghici ◽  
Gabriel Saramet ◽  
...  
Keyword(s):  
Acetic Anhydride ◽  
Phosphorus Oxychloride ◽  
Spectral Studies ◽  
Ethyl Chloroformate ◽  
Anhydrous Aluminum Chloride ◽  
1H And 13C Nmr ◽  
Ft Ir ◽  
Concentrated Sulfuric Acid ◽  
New Compounds

Steiger N-acylation of a-alanine with 4-(4-bromophenylsulfonyl)benzoyl chloride led to 2-[4-(4-bromophenylsulfonyl)benzamido]propanoic acid. This compound underwent intramolecular cyclization in the presence of N-methylmorpholine and ethyl chloroformate or acetic anhydride to the corresponding saturated azlactone. Then acylaminoacylation of dry aromatic hydrocarbons with 2-[4-(4-bromophenylsulfonyl)phenyl]-4-methyloxazol-5(4H)-one or 2-[4-(4-bromophenylsulfonyl) benzamido ]propanoyl chloride in the presence of anhydrous aluminum chloride led to corresponding a-acylamino ketones. These new intermediates were heterocyclized under the action of phosphorus oxychloride or concentrated sulfuric acid in the presence of acetic anhydride to the corresponding oxazoles. The newly synthesized compounds were characterized by spectral studies (FT-IR, UV-Vis, MS, 1H- and 13C-NMR) and elemental analysis. The purity of the new compounds was evaluated by RP-HPLC. The experimental research regarding to the in vitro cytotoxic activity of the new compounds were performed using Daphnia magna bioassay.

Design, Synthesis and Biological Evaluation of Anti-tuberculosis Agents based on Bedaquiline Structure

2020 ◽  
Vol 16 (5) ◽  
pp. 703-714
Author(s):  
Chengjun Wu ◽  
Jinghan Luo ◽  
Mengtong Wu ◽  
Fanzhen Meng ◽  
Zhiqiang Cai ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Atp Synthase ◽  
Docking Study ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Mycobacterium Tuberculosis H37rv ◽  
Inhibitory Activities ◽  
Relationship Of

Background: Bedaquiline is a novel anti-tuberculosis drug that inhibits Mycobacterial ATP synthase. However, studies have found that bedaquiline has serious side effects due to high lipophilicity. Recently, the complete structure of ATP synthase was first reported in the Journal of Science. Objective: The study aimed to design, synthesise and carry out biological evaluation of antituberculosis agents based on the structure of bedaquiline. Methods: The mode of action of bedaquiline and ATP synthase was determined by molecular docking, and a series of low lipophilic bedaquiline derivatives were synthesized. The inhibitory activities of bedaquiline derivatives towards Mycobacterium phlei 1180 and Mycobacterium tuberculosis H37Rv were evaluated in vitro. A docking study was carried out to elucidate the structureactivity relationship of the obtained compounds. The predicted ADMET properties of the synthesized compounds were also analyzed. Results: The compounds 5c3, 6a1, and 6d3 showed good inhibitory activities (MIC=15.62 ug.mL-1). At the same time, the compounds 5c3, 6a1, and 6d3 also showed good drug-like properties through molecular docking and ADMET properties prediction. Conclusion: The results of in vitro anti-tuberculosis activity assays, docking studies and ADMET predictions indicate that the synthesized compounds have potential antifungal activity, with compounds 6a1 being further optimized and developed as lead compounds.

scholarly journals Synthesis of Tetrahydro-2H-[1,3,5]thiadiazine-5-(4-pyridylcarboxamido)-2-thione with antitubercular activity

2004 ◽  
Vol 72 (1) ◽  
pp. 35-41 ◽  
Author(s):  
D. Sriram ◽  
K. Jyothi Mallika ◽  
P. Yogeeswari
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Antitubercular Activity ◽  
Antimycobacterial Activity ◽  
Therapeutic Use ◽  
Tuberculosis H37rv ◽  
Mycobacterium Tuberculosis H37rv ◽  
Radiometric System ◽  
Elemental Analyses ◽  
Derivatives Of

3-Substituted-5-(4-pyridylcarboxamide)tetrahydro-2H-[1,3,5]thiadizine-2-thione derivatives (1-9) were synthesized as derivatives of isoniazid (INH) to overcome the resistance developed with its therapeutic use. The structures were confirmed by their spectral and elemental analyses data. These derivatives revealed higher lipophilicity compared with INH. The antimycobacterial activity of the synthesized compounds and INH was evaluated in vitro against Mycobacterium tuberculosis H37Rv at 6.25 µg/ml in BACTEC 12B medium using the BACTEC 460 radiometric system. The derivatives exhibited antitubercular activity.

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